What controls reactivity of ylides? Computational data show that reactivity in the reactions shown in the scheme is mainly determined by the leaving group ability of the onium group, and this decreases for both intrinsic and thermochemical reasons in the order O>S>N>P. The results are consistent with experimental observations and account for the dearth of examples of phosphorus ylides in these reactions.
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Aggarwal et al. (2005) studied this question.
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